


Pennywise - A Series of Shorts

by PompadourWampus



Category: Harry Potter - J. K. Rowling
Genre: Cross-Posted on Tumblr, Experimental Style, F/M, Original Character(s), Originally Posted on Tumblr, POV First Person, Romance, Self-Insert, Video Game: Harry Potter: Hogwarts Mystery
Language: English
Status: In-Progress
Published: 2019-01-11
Updated: 2019-01-11
Packaged: 2019-10-08 03:24:30
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,056
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17378672
Author URL: https://archiveofourown.org/users/PompadourWampus/pseuds/PompadourWampus
Summary: What came after the Vaults?Telemachus Grimlock knew the what but not the how. Not the specifics anyways.Feelings for Penny weren't in the plans.





	1. Pennywise

**Author's Note:**

  * Inspired by [Sadderdaze](https://archiveofourown.org/external_works/465515) by pogohargreeves. 



> Disclosure: 
> 
> These are a series of experimental shorts. I have no experience writing romance, hence the one-shots mini-series route.
> 
> The following may be used as a backbone or foundation for a full fledged story further down the line.
> 
> This is a work in progress and may contain more edit follow-ups.

**Pennywise**

“I can’t believe this!” shouted someone.

I groaned at the noise and attempted to sit up, but Madam Pomfrey placed her hand on my good shoulder and gently guided me back down onto the cot. I had to settle for decifering the speaker’s identity through sound alone. Recognizing that voice brought me immediate dread. It was Penny, Penny Haywood! 

The Hufflepuff sounded angry, and it got me thinking that Rowan was right. He had warned me, before we embarked on our final journey with the rest of the Mystery Crew, that Penny wasn’t taking well to being excluded from our escapades. Something as critical as the last Cursed Vault would be the tipping point for her, but I had insisted that we needn’t bother Penny any further than potions help. The events of our fifth year were still fresh in my mind despite the two years that have past since then. Out of all of us, Penny had been the one placed in the most precarious of situations. She’d nearly lost her sister, Beatrice, and to add to that, Beatrice could’ve lost Penny at any moment before that.

That realization had been a punch to the gut. I couldn’t fathom the idea of having to soldier up in order to pen down a Notification of Death. Those types of situations brought grown men to tears for a reason.

Ever since then, being around Penny made me feel uneasy. Her pressence brought those thoughts to the forefront of my mind, and I didn’t want to be confronted with the truth. If someone were to die, I, as the oldest soul, would be at fault.

“Penny?” I wheezed, and Madam Pomfrey shushed me more harsher than usual as she rubbed the Essence of Dittany into my swollen right eye.

I could sense that she was tenser than normal. The way she stood hunched over my frame gave that away. Then it clicked. I had asked her to keep my condition under the strictest of wraps.

“Miss Haywood, if you aren’t about to keel over this instance, I suggest you leave,” advised the Medi-Witch.

“But I-” began Penny.

“Now!” Pomfrey yelled, and I winced as I heard the curtains flutter shut once more.

This won’t end well.

* * *

 

“We should’ve taken Penny with us,” muttered Rowan as he stared down at my empty sleeve. "Maybe then-"

I was so very glad at that moment that I’d opted to stay at the Hospital Wing. If one person’s staring was wieghing down on me already, then the eyes of the whole school would flatten me.

"How's Ben holding up?" I quickly cut in.

I really didn't want to spend my time talking about _what ifs_. Words of lament lead to thoughts of regret, as they say.

Rowan frowned, and I sighed. My evasiveness hadn't gone unnoticed. It never did these days.

"Look," I said defensively, right as Rowan pushed his spectacles up the bridge of his nose, "last I saw Ben he was panicking over my lack of arm. I made him keep quiet about it. I didn't want the others to worry."

"Which is something you shouldn't have done," noted Rowan as he extracted _You Can Never Be too Paranoid,_ a book by one _Mayoral Stood_ , from my fidgeting single hold. The Ravenclaw then tossed the book onto my side table, after gleening its authorship from the cover, like it personally offended him. "Really? Another one?"

"You know I swear by his books, Rowan. Wouldn't have gotten through the last two remaining vaults without them," I explained.

Rowan snorted as he shifted his body to rest against the plush chair he'd conjured up for the visit. "Yeah, well, good leaders don't risk their subordinate's sanity over Mayoral Stood rereads. There's no evidence of his existence in the Auror Records of the Wizarding War to even be worth it."

"Good leaders also don't tolerate insubordination," I shot back, and Rowan pursed his lips at that.

He knew I was right but didn't relent until I stared him down.

"Fine," he finally said. "Ben's hauled himself up in Gryffindor Tower. Charlie's told me that he and Jae have had no luck in dragging him out after classes."

"Is it because of-"

"Penny," nodded Rowan. "Penny and Tulip. Mainly those two, but probably Merula as well. Ben's afraid of being grilled by them."

"And you aren't?"

"Nope."

"How'd you manage that? Ravenclaw Tower's practically open season."

"Flitwick."

"Ah."

We fell into an awkward silence after that. It got to the point where Rowan had to physically stand up and pace over to the window between beds in order to give himself something to do. He'd picked up the habit from Talbott Winger, who'd do it whenever he joined our study groups, and left the dividing curtains open just enough so sunlight would carry over along with his voice.

"Telemachus."

"Yeah?"

"I wish you'd learn to live a little. I won't always be around to remind you, you know. Especially not after this year. Who knows where we'll be a year from now. You can't keep treating life like a war."

"It's more like a chore," I joked lightly.

The lack of response highlighted just what Rowan really thought about the matter.

If only he knew what lay ahead. Only then would he embrace doom's day prepping like I did, but then Rowan wouldn't be Rowan. It would make for a dreary time. Parish the thought.


	2. Pennywise Continuation

**Pennywise Continuation**

"Telemachus! Telemachus!" called someone.

I didn't feel like talking to anyone at the moment, so I ignored the voice and sped up my movements down the corridor.

"Telemachus!" they shouted again, this time more loudly.

"What!" I finally snapped.

I would've turned around on the spot if my feet hadn't felt like heavy blocks of lead at that point in time. I could still talk, so it wasn't _immobulus_ that was cast on my person. It was probably _arresto momentum_.

"Can we talk?" the voice asked.

"Ben?" I wondered aloud as the Gryffindor came into view.

Ben gave me a weak smile as he tucked his wand back into his robe pocket, handle pointed upwards.

"Yeah, it's me," he replied in his usual somber.

Well, it would've been his usual somber if his hair weren't so lifeless looking. Everything about him was out of place. The lack of neatly combed hair was just the beginning. The wrinkles on his robes spoke of a day or more gone by without a change of clothes, and for a second, I was tempted to think that it was all an illusion. Sure, Ben had his days, but he hadn't looked like a wreckage since our second year at the very least.

"You're a mess," I noted, and Ben nodded, not even bothering to refute my claim. I frowned. "Ben, what have I told you about not standing up for yourself?"

The Gryffindor straightened out of his slouch upon hearing the tone my voice took. He shot me an apologetic look. "Sorry, but you're not wrong. I am a mess. I couldn't sleep well this past week. And then Penny and Tulip were trying to chase me down after classes, and Merula tried bribing me-"

"She what!"

"Don't act like you're hard of hearing Grimlock! It's as he said," Merula Snyde jeered as she came to a stop behind Ben. I glared at them both, and Ben jumped aside, letting Merula step a foot closer. "Bloody good it did me. Stupid noble Gryffindors. As if refusing a bribe'll stop me from getting what I want."

"Ben!" I hissed, and Ben fumbled about, trying to pull out his wand to undo the spell.

Merula was one step ahead of us both. All it took was one snatch from her hand, and Ben lost possession of his wand right then and there.

"Leave us," she order.

"But-" Ben began. His wide eyes flickered back and forth between us.

"It's alright Ben," I sighed. "I'll handle it."

As soon as those words left my mouth Ben shot off like a rocket down the hall. Now only Merula remained. She pocketed Ben's wand with a satisfied smirk on her face.

"You better uphold your end of the deal, Grimlock. I did as you said and stayed out of the way. I expect full compensation," she proclaimed, and indeed she had.

Merula had not once over stepped her bounds this year. She'd stayed well out of the way, and that was only after I convinced her to leave all the dirty work to us.

The day we came to that agreement I half expected the others to object. No one did. Not even Tulip. Well, Rowan attempted to, but he resigned his objections after being overruled.

At this moment I found myself wishing he hadn't. I'd been counting on Merula forgetting or at the very least Dumbledore stepping it up. The artifacts we found were in the process of being filed and transfered some place else.

"Well? Why aren't you moving?" hissed the Slytherin.

"Maybe try undoing the spell first, why don't ya! Or did you not pick that up?"

Merula's left eye twitched, and with a growl she pulled out her own wand and jabbed it at my neck.

"Careful Grimlock," she intoned, "I could just as easily leave you to rot."

"But you wouldn't," I replied in kind. "You need me to get you where you want to be."

"Why you-"

"Taking hostages are we now, Merula?"

Merula stiffened. Her back's arch was reminiscent of an angered cat as she turned to face the new arrival.

"Karasu," said Merula evenly.

The snide look on her face crumbled under the weight of Tulip's stare.

"This is a new low, even for you," Tulip noted as she crossed her arms.

My eyes sharpened at the action and so did Merula's. Tulip's hands were in perfect position for a quick sleeve draw, and I couldn't help but wonder why she was itching for a duel. Did it really look that bad?

Merula must have recognized that as well, because she quickly stepped away from me. Her wand arm was held out in front of her as she retreated.

"This isn't over," Merula told me as she alternated her aim between Tulip and I. Then she turned around to leave, but Tulip's voice halted her.

"Ben's wand, Merula," the Ravenclaw reminded before the Slytherin could scamper off.

I couldn't hold in the hum of surprise that left my throat. How long had Tulip been there?

Merula sucked her teeth and tossed Ben's wand in the air. "There!" she shouted before bailing out.

"Ben's wand! A fall that high up-"

A silent _Wingardium Leviosa_ had the wand floating to Tulip's outstretched hand, all while she gave me an amused look.

"Or you could do that," I finished lamely.

"Yes, I could," she agreed as she pocketed the rescued wand.

"So, you broke your arm, eh?"

"That's one way of putting it," I stated.

I felt a hand snake up my right sleeve, and I would've tensed if I wasn't already.

"I'm going to undo the spell," Tulip told me as she pulled my robe arm down, "but you better patch things up with Penny."

"Of course."

Once the spell was lifted, relief flooded my body. Tulip nodded at her handy work before spinning around to walk away. Then she paused, tapped her chin in thought, and turned to face me.

"Bit of a warning, but I may or may not be involved in Tonk's next scheme. So you might want to hurry it up a bit."

I had to hold in a groan at the thought. Of course it would be Tonks. Tonks was the nuclear deterrent of our group. If anyone could make us do anything, it was her.


	3. Pennywise Continuation 2

**Pennywise Continuation 2**

"Tonks!" shouted Penny as she steered over to the rowdy metamorphmagus. "That was highly unnessecary!"

"Yeah?"

"Yes!"

"Well so is his brooding!"

"Still! You didn't have to go and turn his hair into a literal bird's nest!"

"Would you have preferred it be a dungbomb instead?" questioned a voice behind them.

Both Tonks and Penny paused in their walking with a start. Tulip had caught up to them with little to no effort.

"No!" Penny replied reflexively as she turned to grab onto the grand stair case's handrail. "I just... I'd prefer it if you two didn't make the situation worse."

Tulip sighed. Her footfalls came to a standstill between the two Hufflepuffs. "I say it can't get any worse than this." The Ravenclaw's hand reached out and bopped the tip of Penny's chin, tearing the blonde's focus away from Hogwarts' stone floors. "Have you taken a look in the mirror recently? You're not looking your best, Penny."

Penny frowned, but didn't object. She knew it was the truth. She hadn't felt like herself in a long while. She was spending more and more sleeplessness nights awake, and for what? Driving herself spare over a potential relationship that was going no where. Maybe it was time to trade in the old traveling cloak. But that would mean conceding defeat.

Had Merula Snyde been right all along? Was she just seeing what she wanted to see?

"Oh no you don't!" barked Tonks.

The sudden noise nearly had Tulip falling off her step and onto the trick step behind them, but Penny had reached out in that instance and gave the redhead an arm to latch onto.

"I know that look!" continued Tonks whilst she stepped closer. They were nearly nose to nose. "You get that look whenever you're considering something those gits told you!"

"Not all Slytherins are-" Penny began as she did her best to hold still while Tulip reeled herself in.

"Barnaby, Liz, and Is- Ismelda are the exception, not the norm!"

"How about we take this somewhere where we don't have the chance to accidentally decapitate ourselves," grumbled a readjusted Tulip as she eased herself between the two.

The stairs beneath their feet settled down again, and Penny realized they'd had a whole discussion on it during two of its turns.

Using Tulip's words as her queue, Penny unwound their arms and lead the way onto the third floor. It was there where she stopped in her movements. The two behind her slipped to either side of her and stopped in their walking as well.

"What else were you planning?" she asked the both of them. Her blue eyes narrowed in the process.

Tonks took on a slouch in posture, and Tulip shot the metamorphmagus a nonplussed look at the reaction. The knot in Penny's stomach tightened.

"Tonks?"

"Alright, fine!" huffed the Hufflepuff flippantly. "Remember that dusty old mirror Dumbledore brought in? The one Filch was polishing?"

"The Mirror of Erised?" supplied Tulip, but by the looks of it, she too was at a loss for what Tonks had done.

Penny took hold of Tonks' robe front and pulled her down so they were at eye level. Her knuckles had gone white with worry.

"Where!" the braid-wearing girl bit out. She'd seen what that mirror was capable of, how it made her feel. It was almost as bad, no, if not worse than, Armortentia. She was sure Tonks knew of that as well. "Where did you put it, Tonks!"

Tonks opened her mouth to refute the harsh treatment, but Penny's hold tightened uncomfortably so. She then looked from the blonde to Tulip, who didn't look one bit as amused as Tonks had felt earlier that day.

"Tonks?" was all the Ravenclaw said. There was no judgement in the redhead's eyes, only concern.

Tonks sighed as she looked away. "I put it in the _office_ , but I meant well with it. I don't think it's- that awful..." Being set free so suddenly had Tonks close to kilting over as Penny ran away.

"Remind me to avoid mirror related pranks at your funeral's post-burial party," commented Tulip.

"Stuff it!" snarked Tonks, feeling the sting of failure. Then some new thoughts tickled her fancy. "But..."

"But?"

"I'll add that to my will."

"Good, then I'll-"

"Also, you're uninvited."

"What! Why?"

"Because you'll be in the coffin with me."

* * *

 

Intent. Penny's father had been big on that when judging actions. Intent. It was something that miffed him when he took one look at British Wizarding law.

Now it had her miffed, but not for the right reasons. She wanted to be mad at Tonks but couldn't find it within herself to have a lasting anger. The initial sparks had dissipated from the bottom pits of her heart, and a feeling of dread had taken its place. Then the familiarity of indignation took over.

All of it could've been avoided if Telemachus hadn't pulled away from her, left her out of the vault proceedings, and used her for solely potions after her fifth year. The frustration that rippled beneath her skin left her feeling exhausted.

Exhaustion. Yes, exhaustion, that was what settled over Penny's heart the moment she reached the open door to Jacob's old office. She contimplated turning right back around and leaving Telemachus to his fate, but the slamming sounds stopped her in her tracks.

"You fucking lied to me!" shouted a hoarse voice.

As Penny stepped through the threshold she took special note at just how out of use the room appeared to be in. Dust floated through the air, and cobwebs crowded the upper corners.

Telemachus wasn't one for disorder, yet there he stood in the middle of it all with his back stiff as a board. Merula, who resembled a furious dragon with her rage, had a withered beater's bat in her hands. A wave of books were spilling off the table that Telemachus was leaning an arm on to keep his balance. His other arm was held outstretched before him in a guard formation like a half boxer readying to take a blow.

No. He had taken a hit already. His sleeve was torn, and something metal like shown through.

"I didn't have a choice in the matter, and even if I did, I still don't know your intentions beyond reaching the vaults," Telemachus said in a clinical fashion.

This not only upset Merula, but it sent a chill down Penny's spine. Whenever the younger Grimlock brother displayed his capability for detachment it always made Penny feel so irrelevant like the gobstones he toyed with when they were first starting out at Hogwarts. Or was she the one feeling detached? Why did she feel so empty?

It was the Ben and Rowan situation all over again, only violenter and with no resolution in sight.

"Lair! You were just bloody stalling you no good traitor! I should've known you'd turn on me just like her!"

Each of Merula's words were emphasized by a swing of the beater's bat, and each time, Telemachus moved his arm around to block. Hollow clanging sounds could be heard more clearly with every hit.

"What were you planning, Merula! How can I trust you when you don't even trust me? It's a freaking two way street!"

Penny knew she should've stepped in. She had her wand out. All she needed was a spell-

"IwAnTeDToPoStBaIL!"

"What!" expressed Telemachus in shock. The very same shock that Penny herself felt at the moment. Her hands trembled in reaction to the pure tragedy occuring before her.

"I. Wanted. To. Set. My. Parents. Free. You. Twat."

The final blow hit a warn down Telemachus in the temple, sending him stumbling through the ricketty table behind him. The remaining books went down with him as the table fell on its side.

Merula jumped back at the noise and dropped the beater's bat as if burned. Then she tried fleeing only to narrowly missing bumping into Penny. That was the last Penny ever saw of the terrified Slytherin.

The image was fleeting, however, and creeking and movement had Penny's focus returning to the person that remained.

"You should stay down," she stated blandly.

"Penny?"

Penny didn't answer. She simply let her actions carry her forward. She felt numb. Two years of numbness reared their ugly heads.

"You kept it..." she muttered in surprise as she crouched down beside Telemachus.

The potions belt she'd given him four years ago was strapped around his waist. She couldn't help brushing her hand against it.

"Handy for duel. Just 'n case," the Ravenclaw slurred.

"Hush, now. The last thing I need is you passing out on me."

And with that, she set to work. The sluggishness didn't go away. It just seeped through.

**Notes for the Chapter:**

> The second half is due for a rewrite. Penny would’ve done something, but I wrote her as out of energy here plus allergic reaction which is expanded upon in the next part. 
> 
> Also, Mirror of Erised is extremely effective as always.
> 
> I’ll rewrite or edit this based on feedback.
> 
> Edit:
> 
> It has been decided that I'll leave things as is.
> 
> Edit:
> 
> Rewrite will be made after series completion.


	4. Pennywise Continuation 3

## Pennywise Continuation 3

I hadn’t thought things through. Not one bit. At least not this time around. Me and my dumb mouth. How could I have forgotten what that stupid mirror did to people? On top of that, how didn’t I figure out the obvious? Merula’s parents were pivotal in her role as a school yard bully. It only made sense that they would influence her choice to go after the Cursed Vaults. She had nothing to lose.

She. Had. Nothing. To. Lose.

“Telemachus,” whispered Penny.

“Huh?”

“I can’t feel my arm.”

I absently rubbed Penny’s back in reply. It didn’t work in soothing the situation, however, as the girl winced in response.

“We’re almost there,” I assured her.

I could feel Penny nodding into my shoulder, and that brought up another concern to the forefront of my mind. What caused Penny to-

“WHY IS MY SISTER BLUE!”

-turn blue?

A groan left Penny’s lips as she burrowed her head deeper into my shoulder.

“Beatrice, could you give us a hand? We’re on our last legs here,” I called the blonde over, “and keep it down with the voices, yeah?”

Beatrice Haywood pouted as she marched right on over. I did my best not to wince as my eardrums continued to ring from her shout. It was a clear sign that my concussion was only half healed. Penny wasn’t a healer after all, only a potioneer.

When we stepped through the Hospital Wing’s doors Madam Pomfrey took one look at us and yanked Penny from our hold. The medi-witch hauled the Hufflepuff onto a bed like a woman gone mad and waved her wand around casting what I assumed were various diagnostic spells.

“Mr. Grimlock! What in the world did you and your companions get yourselves into now!” exclaimed the matron.

“Nothing!” I yelped as I brought a hand to my temple. I felt myself tremble unsteadly for a few seconds. Then someone pulled me still. Peeking over my elbow I saw Beatrice give me an inquiring look.

“Then tell me, Mr. Grimlock, why is it that Miss Haywood is having an allergic reaction to an extremely rare plant that’s practically extinct?”

Just as Madam Pomfrey uttered those words Beatrice’s hand went from steadying me by the sleeve to pinching my upper arm.

“I-I don’t know!” I cried as my mind caved in to the vertigo.

From their, things blurred. A host of thoughts hit me all at once, snuffing out anything that could’ve been legible.

Hours later, I awoke tucked into a bed that sat beside Penny’s. Madam Pomfrey must’ve placed us near each other in order to easily tend to both of us at once. Between us, on a stool, sat Beatrice with her back facing towards me. She was holding her sister’s wrist like it were a delicate flower. The sight sent a guilt ridden pang down my throat. Avoiding the Haywood Sisters was supposed to prevent this scenario from occuring a second time.

“But it didn’t, did it?” said Beatrice.

“What!” I gasped in surprise. Had I said that aloud?

“You know what you said,” Beatrice confirmed.

With that understanding gleaned, my eyes traveled away from Beatrice’s back to the hanging golden fixtures up on the ceiling. I kept quiet for a couple of moments until the prickling pain in my chest boiled over in the form of wet splotches within my vision.

“No,” I croaked.

“Then you know what you gotta do.”

Something wooden creaked, and footsteps could be heard leaving the vicinity. When I turned to look, the stool at Penny’s side was empty. It was tempting, very tempting, to pretend that the whole encounter had occured inside my head, but I knew the truth. It hadn’t, and it hurt.

**Author's Note:**

> The Pennywise Table of Content Link on Tumblr...
> 
> https://pompadourwampus.tumblr.com/post/186073444182/pennywise-table-of-contents
> 
> I tend to upload things on there first when it comes to shorts.


End file.
